Great Wolf of the Air
Unlocked by wearing a moon-amber necklace. This is craftable after you have learned the recipe in the Tower. You can only learn the recipe as a myst class. So, do a myst ascension and you can fight this guy any time.
He does two kinds of attacks. We will call them major and minor.
Major attack comes first and does max HP + 50 - DR. The next time he uses major attack (round 3) it will do 30 more damage. The next time (round 5) it will do an additional 30 damage (so max HP + 50 - DR + 60). And so on.
Minor attack is not fully spaded but responds to buffing Moxie.
As long as you have enough HP to survive a single minor attack, there is no need to buff HP.
Damage in combat will either be done with spells (snowclone, saucegeyser, volcanometeor) or combat items (love songs, cursed voodoo skulls).
Buff DR as much as you can. This directly extends the length of time you can survive. Jarlsberg's pan does not work.
Buff Moxie as much as you can. This will minimize the amount of damage done by the minor attack. This *may* let you skip a round of healing (see below).
Not really buffing, but Funkslinging is really, really helpful.
Equip a Rain-Doh green lantern.
After a major attack you will need to do a full heal. So massage oil or soggy band-aids and a combat item (love songs against lower kiss, cursed voodoo skulls against higher kiss).
If the minor attack does very little damage, you might be able to skip healing that round. If so, use your biggest spell. If not, just do the same as after a major attack.
He is weaker to elemental attacks than to physical. That's why you're using love songs over divines. Cursed voodoo skulls split the damage over 2 elements.
A real bastard if ever there was one.
Unlocked by wearing a Dreadsylvanian auditor badge. This comes from having a replica key in inventory (these are tradeable. Moxie classes make them in the Ticking Shack with a complicated lock impression and intricate music box parts) and then choosing the correct choice in the Cabin. Anyone can get one of these.
Each round he will make a decree. These decrees are either that you be wearing some piece of equipment, that you use some skill, or that you use some combat item.
The list of equipment, skills and combat items is fixed and can be found here.
The equipment is all tradeable.
The combat items are all tradeable except sparking El Vibrato drone and sharpened hubcap (from Hobopolis marketplace).
If you heal in any way you die instantly. In particular this means saucespheres are a bad idea.
His attack is 1000 + 500*number of kisses
His defense is 1000 + 500*number of kisses
His HP is 8000 + 2000*number of kisses
Equip the outfit. I opt for Rain-Doh green lantern over the plush hamsterpus. It gives me a lot more damage from Frigidalmatian and snowclones.
Ambidextrous Funkslinging is really helpful. You can funksling love songs and whatever combat item, when he asks for one.
Buy the combat items. I don't buy hot clusterbombs because they are super expensive.
You may need more than one of each combat item in a combat.
If you really want, acquire Spooky Breath. I skip this one too.
Buff your moxie and HP. You can't heal in combat.
When he asks for a spell, cast it.
When he asks for a piece of equipment, cast Snowclone.
When he asks for a combat item, funksling it and a love song.
Cross your fingers. My record, lacking 4 things (hot clusterbomb, sparking El Vibrato drone, Spooky Breath and hamsterpus), is 17 defeats before finally killing him.
He is unlocked by having the Shepherd's Breath buff active when entering combat. This buff comes from eating a shepherd's pie. The pie parts are tradeable but the pie is not. Only myst classes can make the pie. So, unless you stocked up in a previous ascension, you can only fight him as myst.
The effect is all removed when you win. So doing something like using a PYEC to extend the buff won't let you get multiple boss kills from one pie.
You can't do anything during this fight. No skills, no combat items, nothing. So you enter combat and just try anything. You'll fail and go to the next round.
So how do you kill him? Familiar damage and passive damage.
He has elemental damage caps, so favor physical damage over all else.
Each round he will hit you for around 10% of max HP.
For an easy, in-game cheat sheet, check out Sauciest Saucier (#1873222).
Hat is parasitic headgnawer. Crank this up a notch by also using an unstable DNA.
Offhand is cup of infinite pencils.
Get whatever else you can from this list.
Other biggies include Vent Rage Gland, eel battery and Long Live GORF (which requires stomach space).
Familiar is the last piece of the puzzle. You can go with a high attack fam, like a Scarecrow with lobsterskin pants. You can go with a heavy mosquito (buffed with jingle bells, a potion of punctuality and Loathing Legion helicopter if you have one). Or you could try a 100-lb base Stocking Mimic if you have one of those.
My preference is the mosquito. Everyone has one and it works.
You'll want to lower your HP as much as possible. The debuff from the Fear Man's level does a good job here. As does Majorly Poisoned.
If your HP is low enough, a single mosquito action will extend combat by several rounds. This will give you more time to kill him. Even at 6-kisses this fight is trivial if you prepare correctly.
You can't do anything. Click blindly and succeed